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In resealable plastic bag, combine flank steak and 1/2 cup vinaigrette. Refrigerate for at least 8 hours or up to 24 hours.
Preheat grill to medium-high heat; grease grate well. Shake off excess marinade from steak, discarding marinade. Season steak with pepper; grill steak, turning once, for 8 to 10 minutes for medium-rare, or until cooked as desired. Let stand for 10 minutes. Slice thinly across the grain.
Toss arugula with 1/3 cup vinaigrette; transfer to serving platter. Scatter tomatoes and shallot over top. Arrange steak slices over top. Sprinkle with blue cheese and drizzle with remaining vinaigrette.
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